Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety

Saki Yajima; Tsuyoshi Saitoh; Kohei Kawa; Kensuke Nakamura; Hiroshi Nagase; Yasuaki Einaga; Shigeru Nishiyama

doi:10.1016/j.tet.2016.10.068

Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety

Saki Yajima, Tsuyoshi Saitoh, Kohei Kawa, Kensuke Nakamura, Hiroshi Nagase, Yasuaki Einaga, Shigeru Nishiyama

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

Cyclohexadienone derivatives possessing α-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.

Original language	English
Pages (from-to)	8428-8435
Number of pages	8
Journal	Tetrahedron
Volume	72
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2016.10.068
Publication status	Published - 2016

Keywords

Anodic oxidation
Boron-doped diamond electrodes
Cyclohexadienone
Diastereoselective hydrogenation
Hypervalent iodobenzene

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2016.10.068

Cite this

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title = "Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety",

abstract = "Cyclohexadienone derivatives possessing α-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.",

keywords = "Anodic oxidation, Boron-doped diamond electrodes, Cyclohexadienone, Diastereoselective hydrogenation, Hypervalent iodobenzene",

author = "Saki Yajima and Tsuyoshi Saitoh and Kohei Kawa and Kensuke Nakamura and Hiroshi Nagase and Yasuaki Einaga and Shigeru Nishiyama",

note = "Funding Information: This study was supported by Grants-in-Aid for Scientific Research C, MEXT (Grant 23510262 ), MEXT -Supported Programs for the Strategic Research Foundation at Private Universities (Grant S1201020 ), and ACCEL, JST . Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

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language = "English",

volume = "72",

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journal = "Tetrahedron",

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T1 - Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety

AU - Yajima, Saki

AU - Saitoh, Tsuyoshi

AU - Kawa, Kohei

AU - Nakamura, Kensuke

AU - Nagase, Hiroshi

AU - Einaga, Yasuaki

AU - Nishiyama, Shigeru

N1 - Funding Information: This study was supported by Grants-in-Aid for Scientific Research C, MEXT (Grant 23510262 ), MEXT -Supported Programs for the Strategic Research Foundation at Private Universities (Grant S1201020 ), and ACCEL, JST . Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - Cyclohexadienone derivatives possessing α-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.

AB - Cyclohexadienone derivatives possessing α-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.

KW - Anodic oxidation

KW - Boron-doped diamond electrodes

KW - Cyclohexadienone

KW - Diastereoselective hydrogenation

KW - Hypervalent iodobenzene

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DO - 10.1016/j.tet.2016.10.068

M3 - Article

AN - SCOPUS:84998812249

SN - 0040-4020

VL - 72

SP - 8428

EP - 8435

JO - Tetrahedron

JF - Tetrahedron

IS - 51

ER -

Asymmetric induction in cyclohexadienones carrying α-D-glucopyranosyl moiety

Abstract

Keywords

ASJC Scopus subject areas

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